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Green and chemoselective synthesis of pyrazolo[3,4-e][1,4]thiazepines and evaluation of their anti-infective activities

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Abstract

A green and convenient approach to the synthesis of medicinally valuable pyrazolo[3,4-e][1,4]thiazepines via three-component reaction of appropriate aldehydes, 5-amino-3-methylpyrazole, and α-mercaptocarboxylic acids in water under sonication is described. This new protocol provides, via chemoselective synthesis, a new heptacyclic ring system instead of the expected pentacyclic ring system. Experimental simplicity, good functional group tolerance, excellent yields, short routine, and selectivity without the need of a catalyst are prominent features of this sonocatalyzed procedure. The representative compounds were screened for their in vitro anti-bacterial and anti-tubercular activities.

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Acknowledgments

Financial assistance from the C.S.I.R, New Delhi is gratefully acknowledged. We are also grateful to the Central Drug Research Institute (CDRI), Lucknow and the SAIF, Kochi, for spectral analyses and elemental analyses, and Microcare Laboratory, Surat, for providing various biological screening analyses.

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Authors and Affiliations

  1. Department of Chemistry, University of Rajasthan, Jaipur, India

    Anshu Dandia & Ruby Singh

  2. Department of Chemistry, Malaviya National Institute of Technology, Jaipur, India

    Jyoti Joshi & Shuchi Maheshwari

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  1. Anshu Dandia
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  2. Ruby Singh
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  4. Shuchi Maheshwari
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Correspondence to Anshu Dandia.

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Dandia, A., Singh, R., Joshi, J. et al. Green and chemoselective synthesis of pyrazolo[3,4-e][1,4]thiazepines and evaluation of their anti-infective activities. Res Chem Intermed 41, 4213–4226 (2015). https://doi.org/10.1007/s11164-013-1524-2

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